Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones‡

文献情報

出版日 2020-12-21

DOI 10.1039/D0QO01410A

インパクトファクター 5.281

著者

Fan-Lin Zeng, Xiao-Lan Chen, Kai Sun, Hu-Lin Zhu, Xiao-Ya Yuan, Ling-Bo Qu, Yu-Fen Zhao, Bing Yu

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要旨

Photocatalytic strategies for the preparation of 3-phosphoryl/trifluoromethyl/thiocyanato azaspiro[4.5]trienones via a radical-initiated cascade annulation reaction of N-arylpropiolamides with phosphorus reagents, 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one (Togni's reagent II) or NH4SCN have been developed under blue LED irradiation at room temperature. The novel synthetic methodologies constitute the first application of 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) as a photocatalyst for the synthesis of spiro-γ-lactam derivatives, in which the use of transition metals and a high reaction temperature could be avoided. The reactions are operationally simple, easy to scale up, and metal-free with wide reaction scope and good functional group tolerance.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones‡

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